136265-10-6

Upstream product

• 459-32-5 4-fluorocinnamic acid 
• 64-17-5 ethanol 
• 140-88-5 ethyl acrylate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 133505-33-6 carbethoxymethyldibutyltelluronium bromide 
• 38788-38-4 dibutyl telluride 
• 105-36-2 ethyl bromoacetate 
• 141-78-6 ethyl acetate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 462-06-6 fluorobenzene 
• 2033-24-1 cycl-isopropylidene malonate 
• 141-82-2 malonic acid 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 

Downstream Products

• 7116-38-3 ethyl 3-(4-fluorophenyl)propanoate 
• 1093858-31-1 C₂₆H₂₂F₂N₂O₄ 
• 116608-92-5 5-(4-Fluoro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 92712-82-8 5-(4-fluorobenzyl)-2-methylthio-4-pyrimidone 
• 116608-84-5 5-(4-Fluoro-benzyl)-2-[2-(5-methyl-1H-imidazol-4-ylmethylsulfanyl)-ethylamino]-1H-pyrimidin-4-one; hydrochloride 
• 162549-00-0 4-fluoro-β-methylbenzenepropanoic acid ethyl ester 
• 463934-02-3 phosphoric acid diethyl ester 3-(4-fluorophenyl)allyl ester 
• 6992-87-6 1-(4-fluorophenyl)-3-bromoprop-1-ene 
• 459-32-5 4-fluorocinnamic acid 
• 166045-40-5 2-(4-fluorophenyl)-2,3-dihydro-4H-1-benzothiopyran-4-one 

Relevant academic research and scientific papers

Atomically precise palladium nanocluster catalyzed tandem oxidation processes of alcohols and phosphorous ylides: Facile access to α,β-unsaturated esters

The mesoporous silica nanosphere supported palladium nanocluster was synthesized through a simple impregnation method and well characterized. The as prepared catalyst shows excellent catalytic performance in tandem oxidation process (TOP) of alcohol and phosphorous ylide, which provides an efficient access to α,β-unsaturated esters with high yields utilizes 1 atmosphere of molecular oxygen as sole oxidant. This work represents the first example of atomically precise palladium nanocluster catalyzed tandem oxidation process of alcohol and phosphorous ylide and is expected to open new horizons for nanoclusters in the tandem reactions.

Palladium-catalyzed conversion of aldehydes to alkenes in the presence of tri-n-butylphosphine

Palladium-catalyzed conversion of aldehydes to alkenes in the presence of tri-n-butylphosphine is described.

Synthesis and in vitro evaluation of antimycobacterial and cytotoxic activity of new α,β-unsaturated amide, oxazoline and oxazole derivatives from L-serine

The synthesis of 19 compounds derived from L-serine and analogs of p-substituted cinnamic acid is reported. Oxazolines 9 and oxazoles 10 have high antitubercular activity with Minimum Inhibitory Concentration (MIC) of 0.7812–25.0 μg/mL (3.21–100.3 μM), against two strains of Mycobacterium tuberculosis sensitive to first-line drugs Isoniazid (INH), Rifampicin (RIF), Ethambutol (EMB), Pyrazinamide (PZE) (H37Rv) and a clinical isolate resistant to INH, RIF and EMB (G122). The cytotoxic evaluation shows that oxazoles have low activity, finding viability>96% against the VERO cell line. The results show these compounds could be considered as future alternatives for antitubercular treatment.

A One-Pot Synthesis of α,β-Unsaturated Esters From Esters

A convenient method for reductive Horner–Wadsworth–Emmons (HWE) olefination is described. The E-selective HWE homologation of various esters to α,β-unsaturated esters was readily achieved and gave the desired products in good-to-moderate yields under mild conditions. The one-pot reaction proceeds through an in situ generated aldehyde, formed via the partial reduction of an ester with lithium diisobutyl-t-butoxyaluminum hydride. The formation of cyclized metal acetal and subsequent decompose to the aldehyde for the olefination was found to be a crucial step in this C2-carbon homologation protocol.

Quantitative Structure-Property Relationship (QSPR) models for a local quantum descriptor: Investigation of the 4- and 3-substituted-cinnamic acid esterification

In this work, the theoretical description of the 4- and 3-substituted-cinnamic acid esterification with different electron donating and electron withdrawing groups was performed at the B3LYP and M06-2X levels, as a two-step process: the O-protonation and the nucleophile attack by ethanol. In parallel, an experimental work devoted to the synthesis and characterization of the substituted-cinnamate esters has also been performed. In order to quantify the substituents effects, quantitative structure-property relationship (QSPR) models based on the atomic charges, Fukui functions and the Frontier Effective-for-Reaction Molecular Orbitals (FERMO) energies were investigated. In fact, the Fukui functions, f+C and f-O, indicated poor correlations for each individual step, and in contrast with the general literature, the O-protonation step is affected both by the FERMO energies and the O-charges of the carbonyl group. Since the process was shown to not be totally described by either charge- or frontier-orbitals, it is proposed to be frontier-charge-miscere controlled. Moreover, the observed trend for the experimental reaction yields suggests that the electron withdrawing groups favor the reaction and the same was observed for Step 2, which can thus be pointed out as the determining step.

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

Identification of (6S)-cyclopropyl-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamines as new HBV capsid assembly modulators

GYH2-18 is a type II HBV CAM with 6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamine (DPPC) skeleton discovered by Roche INC. A series of GYH2-18 derivatives were designed, synthesized and evaluated for their anti-HBV activity. Two compounds 2f and 3k exhibited excellent anti-HBV activity, low cytotoxicity and accepted oral PK profiles. Chiral separation of 2f and 3k was conducted successfully, and (6S)-cyclopropyl DPPC isomers 2f-1, 2f-3, 3k-1 and 3k-3 were identified to be much more active than the corresponding (6R)-ones. The preliminary structure-activity relationship, particle gel assay and molecular modeling studies were also discussed, which provide useful indications for guiding the further rational design of new (6S)-cyclopropyl DPPC analogues.

Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones

Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem is thermal proteome profiling (TPP), which determines the effect of an unmodified small molecule on the thermal stability of the whole proteome simultaneously. Here, we use TPP to identify the mode-of-action of a newly-discovered autophagy inhibitor based on oxazolidinones often employed as chiral auxiliaries. Surprisingly, a significant portion of all ribosomal proteins were found to be destabilized by the inhibitor, highlighting the utility of this technology for determining a challenging mode-of-action.

Electrochemical Generation of a Nonstabilized Azomethine Ylide: Access to Substituted N-Heterocycles

Azomethine ylides are fascinating 1,3-dipoles for [3 + 2] cycloaddition reactions toward the construction ofN-heterocycles. Herein, an efficient and environmentally benign electrochemical approach for the generation of a nonstabilized azomethine ylide has been established under metal-free and external oxidant-free conditions. The resulting 1,3-dipole undergoes a [3 + 2] cycloaddition reaction with olefins. This electrosynthetic methodology indulges a straightforward and facile approach for the construction of substituted pyrrolidines.

Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae)

Cinnamic acid derivatives (CAD's) represent a great alternative in the search for insecticides against Aedes aegypti mosquitoes since they have antimicrobial and insecticide properties. Ae. aegypti is responsible for transmitting Dengue, Chikungunya, and Zika viruses, among other arboviruses associated with morbimortality, especially in developing countries. In view of this, in vitro analyses of n-substituted cinnamic acids and esters were performed upon 4th instar larvae (L4) of Ae. aegypti, as well as, molecular docking studies to propose a potential biological target towards this mosquitoes species. The larvicide assays proved that n-substituted ethyl cinnamates showed a more pronounced activity than their corresponding acids, in which p-chlorocinnamate (3j) presented a LC50 value of 8.3 μg/mL. Thusly, external morphologic alterations (rigid and elongated body, curved bowel, and translucent or darkened anal papillae) of mosquitoes’ group exposed to compound 3j, were observed by microscopy. In addition, an analytical method was developed for the quantification of the most promising analog by using high-performance liquid chromatography with UV detection (HPLC-UV). Molecular docking studies suggested that the larvicide action is associated with inhibition of acetylcholinesterase (AChE) enzyme. Therefore, expanding the larvicidal study with the cinnamic acid derivatives against the vector Ae. aegypti is important for finding search for more effective larvicides and with lower toxicity, since they have already shown good larvicidal properties against Ae. aegypti.